title: Chemistry of mycolactones, the causative toxins of Buruli ulcer.
abstract: Buruli ulcer is a severe and devastating skin disease caused by Mycobacterium ulcerans infection, yet it is one of the most neglected diseases. The causative toxin, referred to as mycolactone A/B, was isolated and characterized as a polyketide-derived macrolide in 1999. The current status of the mycolactone chemistry is described, highlighting the stereochemistry assignment of mycolactone A/B; total synthesis; the structure determination of mycolactone congeners from the human pathogen M. ulcerans, the frog pathogen Mycobacterium liflandii, and the fish pathogen Mycobacterium marinum; the structural diversity in the mycolactone class of natural products; the highly sensitive detection/structure-analysis of mycolactones; and some biological activity.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA. kishi@chemistry.harvard.edu
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Kishi
mesh_terms: D000818:Animals; D001001:Anura; D001427:Bacterial Toxins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity; D054312:Buruli Ulcer / Q000139:chemically induced / Q000382:microbiology* / Q000473:pathology; D005393:Fish Diseases / Q000382:microbiology / Q000473:pathology; D005399:Fishes; D006168:Guinea Pigs; D006801:Humans; D018942:Macrolides; D015394:Molecular Structure; D019911:Mycobacterium ulcerans / Q000737:chemistry* / Q000472:pathogenicity
chemical_list: D001427:Bacterial Toxins; D018942:Macrolides; C117218:mycolactone